Hydrochloric Acid → N-Carbobenzoxysarcosine

HRID 2175572Notes

Reaction equation

HRID 2175572 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH3:18])[CH2:12][C:13]([O:15]CC)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.[Li+].[OH-].Cl>CO>[CH2:1]([O:8][C:9]([N:11]([CH3:18])[CH2:12][C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 58562640Ethyl 2-(((benzyloxy)carbonyl)(methyl)amino)acetate

Product 1

HCID 97053N-Carbobenzoxysarcosine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 2-(((benzyloxy)carbonyl)(methyl)amino)acetate (2.66 mg, 10.6 mmol, prepared the previous step) in MeOH (24 mL) and THF (5 mL) and treated with a solution of LiOH (12 mL, 54 mmol, 4.52 M in water). After stirring at room temperature for 3 hours, the pH was adjusted to ˜5 by the addition of aqueous HCl. After extraction with ethyl acetate, the organic layer was dried over Na2SO4 and concentrated in vacuo to yield the product.

Workup

  1. extractionAfter extraction with ethyl acetate
  2. dry with materialthe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customto yield the product

Sources & evidence

ORD record
ord-f8c3d75ec9ab426897e888ef2b5570d7
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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